3-(dimethylaminomethyl)benzonitrile → 1-[3-(Aminomethyl)phenyl]-N,N-dimethylmethanamine

HRID 1804549Notes

Reaction equation

HRID 1804549 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])[CH3:3]>N.[Ni]>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])[CH3:1]

Participants

4

Reactant 1

HCID 46410883-(dimethylaminomethyl)benzonitrile

Product 1

HCID 162280701-[3-(Aminomethyl)phenyl]-N,N-dimethylmethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

7.00 g (34.95 mmol) 3-dimethylaminomethyl-benzonitrile are placed in 100 ml of methanolic ammonia solution and hydrogenated with 1.40 g Raney nickel at ambient temperature under a pressure of 3 bar. The catalyst is suction filtered, the filtrate is evaporated down. The residue is purified by chromatography.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-cc3e026be93e4d69bbb85eddd8afeb61
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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